#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/36/4513631.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4513631
loop_
_publ_author_name
'Pang, Xue'
'Wang, Hui'
'Wang, Weizhou'
'Jin, Wei Jun'
_publ_section_title
;
 Phosphorescent π-Hole···π Bonding Cocrystals of
 Pyrene with Halo-perfluorobenzenes (F, Cl, Br, I)
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4938
_journal_paper_doi               10.1021/acs.cgd.5b00844
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C22 H10 Br F5'
_chemical_formula_weight         449.21
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.993(5)
_cell_angle_beta                 105.843(6)
_cell_angle_gamma                90.323(6)
_cell_formula_units_Z            4
_cell_length_a                   9.155(3)
_cell_length_b                   13.793(4)
_cell_length_c                   13.924(5)
_cell_measurement_reflns_used    1476
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      2.96
_cell_volume                     1690.2(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0880
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8249
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    2.489
_exptl_absorpt_correction_T_max  0.7379
_exptl_absorpt_correction_T_min  0.4212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_refine_diff_density_max         2.736
_refine_diff_density_min         -0.967
_refine_diff_density_rms         0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         6009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0753
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1309P)²+0.5286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1899
_refine_ls_wR_factor_ref         0.2154
_reflns_number_gt                3970
_reflns_number_total             6009
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00844_si_001.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4513628--4513635.cif.
;
_cod_original_cell_volume        1690.2(9)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4513631
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.54935(10) 0.76346(5) 0.26469(6) 0.0273(3) Uani 1 1 d .
Br2 Br 0.03838(11) 0.71531(6) 0.26851(6) 0.0318(3) Uani 1 1 d .
C1 C 0.5220(9) 0.8965(6) 0.2560(5) 0.0222(17) Uani 1 1 d .
C2 C 0.6378(8) 0.9610(5) 0.2916(5) 0.0184(16) Uani 1 1 d .
C3 C 0.6210(9) 1.0596(6) 0.2840(5) 0.0213(17) Uani 1 1 d .
C4 C 0.4775(9) 1.0953(5) 0.2374(5) 0.0215(17) Uani 1 1 d .
C5 C 0.3577(8) 1.0315(6) 0.2010(5) 0.0215(17) Uani 1 1 d .
C6 C 0.3793(9) 0.9338(6) 0.2104(5) 0.0220(17) Uani 1 1 d .
C7 C 0.0127(9) 0.5801(5) 0.2561(6) 0.0223(17) Uani 1 1 d .
C8 C -0.1270(9) 0.5371(5) 0.2102(5) 0.0199(16) Uani 1 1 d .
C9 C -0.1437(8) 0.4382(6) 0.2021(5) 0.0229(17) Uani 1 1 d .
C10 C -0.0230(8) 0.3796(5) 0.2394(5) 0.0170(16) Uani 1 1 d .
C11 C 0.1192(8) 0.4219(5) 0.2844(5) 0.0198(16) Uani 1 1 d .
C12 C 0.1362(8) 0.5214(5) 0.2938(5) 0.0189(16) Uani 1 1 d .
C13 C 0.5022(9) 0.1851(5) 0.0004(5) 0.0228(18) Uani 1 1 d .
H13 H 0.4788 0.2518 -0.0082 0.027 Uiso 1 1 calc R
C14 C 0.6421(10) 0.1611(5) 0.0467(6) 0.0234(18) Uani 1 1 d .
H14 H 0.7152 0.2115 0.0716 0.028 Uiso 1 1 calc R
C15 C 0.6899(9) 0.0616(6) 0.0615(5) 0.0229(18) Uani 1 1 d .
C16 C 0.8366(9) 0.0357(6) 0.1076(5) 0.0260(18) Uani 1 1 d .
H16 H 0.9130 0.0844 0.1311 0.031 Uiso 1 1 calc R
C17 C 0.8731(10) -0.0611(6) 0.1199(6) 0.030(2) Uani 1 1 d .
H17 H 0.9749 -0.0776 0.1521 0.036 Uiso 1 1 calc R
C18 C 0.7669(9) -0.1337(6) 0.0870(6) 0.0276(19) Uani 1 1 d .
H18 H 0.7953 -0.1994 0.0979 0.033 Uiso 1 1 calc R
C19 C 0.6186(9) -0.1122(5) 0.0383(5) 0.0214(17) Uani 1 1 d .
C20 C 0.5738(8) -0.0129(5) 0.0237(5) 0.0179(16) Uani 1 1 d .
C21 C -0.1882(10) 0.3581(6) -0.0548(6) 0.0264(19) Uani 1 1 d .
H21 H -0.2746 0.3173 -0.0817 0.032 Uiso 1 1 calc R
C22 C -0.0548(9) 0.3176(5) -0.0099(5) 0.0215(17) Uani 1 1 d .
H22 H -0.0501 0.2491 -0.0053 0.026 Uiso 1 1 calc R
C23 C 0.0822(9) 0.3757(5) 0.0319(5) 0.0220(17) Uani 1 1 d .
C24 C 0.2202(10) 0.3366(6) 0.0793(6) 0.0269(19) Uani 1 1 d .
H24 H 0.2288 0.2685 0.0865 0.032 Uiso 1 1 calc R
C25 C 0.3463(10) 0.3965(6) 0.1163(6) 0.031(2) Uani 1 1 d .
H25 H 0.4408 0.3679 0.1473 0.037 Uiso 1 1 calc R
C26 C 0.3398(9) 0.4962(6) 0.1098(5) 0.0257(18) Uani 1 1 d .
H26 H 0.4281 0.5352 0.1372 0.031 Uiso 1 1 calc R
C27 C 0.2038(9) 0.5385(6) 0.0633(6) 0.0248(18) Uani 1 1 d .
C28 C 0.0704(8) 0.4791(5) 0.0233(5) 0.0172(16) Uani 1 1 d .
C29 C 0.6320(9) 0.1646(5) 0.5187(5) 0.0223(17) Uani 1 1 d .
H29 H 0.7024 0.2175 0.5337 0.027 Uiso 1 1 calc R
C30 C 0.4876(9) 0.1815(5) 0.4724(5) 0.0186(16) Uani 1 1 d .
H30 H 0.4575 0.2459 0.4556 0.022 Uiso 1 1 calc R
C31 C 0.3756(8) 0.1040(5) 0.4469(5) 0.0178(16) Uani 1 1 d .
C32 C 0.2234(9) 0.1191(6) 0.3966(5) 0.0216(17) Uani 1 1 d .
H32 H 0.1915 0.1823 0.3758 0.026 Uiso 1 1 calc R
C33 C 0.1189(9) 0.0431(6) 0.3767(6) 0.0257(18) Uani 1 1 d .
H33 H 0.0156 0.0547 0.3433 0.031 Uiso 1 1 calc R
C34 C 0.1631(9) -0.0491(6) 0.4050(5) 0.0221(17) Uani 1 1 d .
H34 H 0.0893 -0.1001 0.3915 0.027 Uiso 1 1 calc R
C35 C 0.3148(9) -0.0696(5) 0.4533(5) 0.0229(18) Uani 1 1 d .
C36 C 0.4220(8) 0.0094(5) 0.4750(5) 0.0176(16) Uani 1 1 d .
C37 C -0.1319(8) 0.6628(5) 0.4830(5) 0.0189(16) Uani 1 1 d .
H37 H -0.2017 0.7146 0.4685 0.023 Uiso 1 1 calc R
C38 C 0.0159(9) 0.6827(5) 0.5298(5) 0.0216(17) Uani 1 1 d .
H38 H 0.0470 0.7482 0.5477 0.026 Uiso 1 1 calc R
C39 C 0.1266(8) 0.6081(5) 0.5531(5) 0.0170(16) Uani 1 1 d .
C40 C 0.2796(9) 0.6264(5) 0.6022(5) 0.0210(17) Uani 1 1 d .
H40 H 0.3120 0.6911 0.6237 0.025 Uiso 1 1 calc R
C41 C 0.3848(9) 0.5535(5) 0.6204(5) 0.0218(17) Uani 1 1 d .
H41 H 0.4888 0.5682 0.6516 0.026 Uiso 1 1 calc R
C42 C 0.3368(9) 0.4569(6) 0.5923(5) 0.0249(18) Uani 1 1 d .
H42 H 0.4088 0.4063 0.6056 0.030 Uiso 1 1 calc R
C43 C 0.1849(8) 0.4347(5) 0.5451(5) 0.0176(16) Uani 1 1 d .
C44 C 0.0772(8) 0.5103(5) 0.5238(5) 0.0186(16) Uani 1 1 d .
F1 F 0.7782(5) 0.9283(3) 0.3383(3) 0.0282(11) Uani 1 1 d .
F2 F 0.7383(5) 1.1217(3) 0.3188(3) 0.0293(11) Uani 1 1 d .
F3 F 0.4601(5) 1.1912(3) 0.2324(3) 0.0287(11) Uani 1 1 d .
F4 F 0.2210(5) 1.0671(3) 0.1562(3) 0.0279(11) Uani 1 1 d .
F5 F 0.2590(5) 0.8731(3) 0.1728(3) 0.0297(11) Uani 1 1 d .
F6 F -0.2499(5) 0.5931(3) 0.1729(3) 0.0318(11) Uani 1 1 d .
F7 F -0.2819(5) 0.3975(3) 0.1565(3) 0.0326(11) Uani 1 1 d .
F8 F -0.0399(5) 0.2836(3) 0.2306(3) 0.0283(11) Uani 1 1 d .
F9 F 0.2380(5) 0.3653(3) 0.3204(3) 0.0277(10) Uani 1 1 d .
F10 F 0.2736(5) 0.5628(3) 0.3392(3) 0.0293(11) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 117.3(7) . .
C2 C1 Br1 122.2(6) . .
C6 C1 Br1 120.5(6) . .
C1 C2 F1 119.4(7) . .
C1 C2 C3 123.2(7) . .
F1 C2 C3 117.3(7) . .
F2 C3 C2 121.9(7) . .
F2 C3 C4 119.5(7) . .
C2 C3 C4 118.6(7) . .
F3 C4 C5 121.8(7) . .
F3 C4 C3 118.7(7) . .
C5 C4 C3 119.5(7) . .
F4 C5 C6 121.3(7) . .
F4 C5 C4 118.6(7) . .
C6 C5 C4 120.0(7) . .
F5 C6 C5 118.4(7) . .
F5 C6 C1 120.2(7) . .
C5 C6 C1 121.4(7) . .
C8 C7 C12 118.9(7) . .
C8 C7 Br2 121.6(6) . .
C12 C7 Br2 119.5(6) . .
F6 C8 C9 119.2(7) . .
F6 C8 C7 120.0(7) . .
C9 C8 C7 120.8(7) . .
F7 C9 C10 119.4(7) . .
F7 C9 C8 119.8(7) . .
C10 C9 C8 120.8(7) . .
F8 C10 C9 120.5(7) . .
F8 C10 C11 120.4(6) . .
C9 C10 C11 119.1(7) . .
F9 C11 C12 120.2(7) . .
F9 C11 C10 119.6(7) . .
C12 C11 C10 120.3(7) . .
F10 C12 C11 120.4(6) . .
F10 C12 C7 119.5(7) . .
C11 C12 C7 120.1(7) . .
C14 C13 C19 122.1(7) . 2_655
C14 C13 H13 119.0 . .
C19 C13 H13 119.0 2_655 .
C13 C14 C15 123.2(7) . .
C13 C14 H14 118.4 . .
C15 C14 H14 118.4 . .
C16 C15 C14 123.7(7) . .
C16 C15 C20 119.9(7) . .
C14 C15 C20 116.4(7) . .
C15 C16 C17 120.2(8) . .
C15 C16 H16 119.9 . .
C17 C16 H16 119.9 . .
C18 C17 C16 121.9(8) . .
C18 C17 H17 119.1 . .
C16 C17 H17 119.1 . .
C17 C18 C19 120.6(8) . .
C17 C18 H18 119.7 . .
C19 C18 H18 119.7 . .
C18 C19 C20 120.1(7) . .
C18 C19 C13 124.3(7) . 2_655
C20 C19 C13 115.6(7) . 2_655
C20 C20 C19 122.5(8) 2_655 .
C20 C20 C15 120.1(8) 2_655 .
C19 C20 C15 117.4(7) . .
C22 C21 C27 121.9(8) . 2_565
C22 C21 H21 119.0 . .
C27 C21 H21 119.0 2_565 .
C21 C22 C23 121.9(7) . .
C21 C22 H22 119.1 . .
C23 C22 H22 119.1 . .
C24 C23 C28 119.3(7) . .
C24 C23 C22 123.3(7) . .
C28 C23 C22 117.4(7) . .
C23 C24 C25 120.1(8) . .
C23 C24 H24 120.0 . .
C25 C24 H24 120.0 . .
C26 C25 C24 122.5(8) . .
C26 C25 H25 118.8 . .
C24 C25 H25 118.8 . .
C27 C26 C25 119.4(8) . .
C27 C26 H26 120.3 . .
C25 C26 H26 120.3 . .
C26 C27 C28 120.0(7) . .
C26 C27 C21 122.5(8) . 2_565
C28 C27 C21 117.6(7) . 2_565
C28 C28 C27 120.9(8) 2_565 .
C28 C28 C23 120.3(8) 2_565 .
C27 C28 C23 118.8(7) . .
C30 C29 C35 122.3(7) . 2_656
C30 C29 H29 118.8 . .
C35 C29 H29 118.8 2_656 .
C29 C30 C31 121.4(7) . .
C29 C30 H30 119.3 . .
C31 C30 H30 119.3 . .
C32 C31 C36 118.9(7) . .
C32 C31 C30 122.8(7) . .
C36 C31 C30 118.3(7) . .
C33 C32 C31 120.7(7) . .
C33 C32 H32 119.6 . .
C31 C32 H32 119.6 . .
C34 C33 C32 120.6(8) . .
C34 C33 H33 119.7 . .
C32 C33 H33 119.7 . .
C33 C34 C35 121.5(7) . .
C33 C34 H34 119.3 . .
C35 C34 H34 119.3 . .
C34 C35 C36 117.7(7) . .
C34 C35 C29 123.8(7) . 2_656
C36 C35 C29 118.4(7) . 2_656
C31 C36 C35 120.5(7) . .
C31 C36 C36 120.5(8) . 2_656
C35 C36 C36 119.0(8) . 2_656
C38 C37 C43 121.2(7) . 2_566
C38 C37 H37 119.4 . .
C43 C37 H37 119.4 2_566 .
C37 C38 C39 122.1(7) . .
C37 C38 H38 119.0 . .
C39 C38 H38 119.0 . .
C40 C39 C44 118.9(7) . .
C40 C39 C38 123.3(7) . .
C44 C39 C38 117.8(7) . .
C41 C40 C39 121.9(7) . .
C41 C40 H40 119.0 . .
C39 C40 H40 119.0 . .
C40 C41 C42 119.5(7) . .
C40 C41 H41 120.3 . .
C42 C41 H41 120.3 . .
C43 C42 C41 120.7(7) . .
C43 C42 H42 119.6 . .
C41 C42 H42 119.6 . .
C42 C43 C44 119.8(7) . .
C42 C43 C37 122.2(7) . 2_566
C44 C43 C37 118.0(7) . 2_566
C44 C44 C43 120.9(8) 2_566 .
C44 C44 C39 119.9(9) 2_566 .
C43 C44 C39 119.1(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.857(8) .
Br2 C7 1.874(7) .
C1 C2 1.354(11) .
C1 C6 1.397(11) .
C2 F1 1.359(8) .
C2 C3 1.373(11) .
C3 F2 1.341(8) .
C3 C4 1.398(11) .
C4 F3 1.335(8) .
C4 C5 1.375(11) .
C5 F4 1.341(9) .
C5 C6 1.368(11) .
C6 F5 1.353(8) .
C7 C8 1.384(11) .
C7 C12 1.388(10) .
C8 F6 1.361(8) .
C8 C9 1.369(11) .
C9 F7 1.359(9) .
C9 C10 1.367(11) .
C10 F8 1.329(8) .
C10 C11 1.396(11) .
C11 F9 1.336(8) .
C11 C12 1.378(10) .
C12 F10 1.356(8) .
C13 C14 1.317(11) .
C13 C19 1.466(11) 2_655
C13 H13 0.9500 .
C14 C15 1.447(11) .
C14 H14 0.9500 .
C15 C16 1.377(11) .
C15 C20 1.452(10) .
C16 C17 1.382(12) .
C16 H16 0.9500 .
C17 C18 1.368(12) .
C17 H17 0.9500 .
C18 C19 1.380(11) .
C18 H18 0.9500 .
C19 C20 1.438(11) .
C19 C13 1.466(11) 2_655
C20 C20 1.387(15) 2_655
C21 C22 1.345(12) .
C21 C27 1.440(11) 2_565
C21 H21 0.9500 .
C22 C23 1.453(11) .
C22 H22 0.9500 .
C23 C24 1.378(11) .
C23 C28 1.437(10) .
C24 C25 1.383(12) .
C24 H24 0.9500 .
C25 C26 1.382(12) .
C25 H25 0.9500 .
C26 C27 1.380(11) .
C26 H26 0.9500 .
C27 C28 1.435(11) .
C27 C21 1.440(11) 2_565
C28 C28 1.412(15) 2_565
C29 C30 1.329(11) .
C29 C35 1.430(11) 2_656
C29 H29 0.9500 .
C30 C31 1.442(10) .
C30 H30 0.9500 .
C31 C32 1.399(11) .
C31 C36 1.410(11) .
C32 C33 1.385(11) .
C32 H32 0.9500 .
C33 C34 1.374(11) .
C33 H33 0.9500 .
C34 C35 1.403(11) .
C34 H34 0.9500 .
C35 C36 1.429(10) .
C35 C29 1.430(11) 2_656
C36 C36 1.437(15) 2_656
C37 C38 1.353(11) .
C37 C43 1.432(10) 2_566
C37 H37 0.9500 .
C38 C39 1.431(10) .
C38 H38 0.9500 .
C39 C40 1.398(10) .
C39 C44 1.431(10) .
C40 C41 1.378(11) .
C40 H40 0.9500 .
C41 C42 1.409(11) .
C41 H41 0.9500 .
C42 C43 1.393(11) .
C42 H42 0.9500 .
C43 C44 1.422(10) .
C43 C37 1.432(10) 2_566
C44 C44 1.409(15) 2_566
